Various forms of media have long been supported by advertising as part of a broader social agreement in which the public gains access to monetarily free or subsidized content in exchange for paying attention to advertising. In print- and broadcast-oriented media distribution systems, advertisers relied on broad audience demographics of various publications and programs in order to target their offers to the appropriate groups of people. The shift to distributing media on the World Wide Web has vastly altered the underlying dynamic by which advertisements are targeted. Rather than rely on imprecise demographics, the online behavioral advertising (OBA) industry has developed a system by which individuals’ web browsing histories are covertly surveilled in order that their product preferences may be deduced from their online behavior. Due to a failure of regulation, Internet users have virtually no means to control such surveillance, and it contravenes a host of well-established social norms. This dissertation explores the ways in which the recent emergence of OBA has come into conflict with these societal norms. Rather than a mere process for targeting messages, OBA represents a profound shift in the underlying balance of power within society. This power balance is embedded in an information asymmetry which gives corporations and governments significantly more knowledge of, and power over, citizens than vice-versa. Companies do not provide the public with an accounting of their techniques or the scale at which they operate. In order to shed light on corporate behavior in the OBA sector, two new tools were developed for this dissertation: webXray and policyXray. webXray is the most powerful tool available for attributing the flow of user data on websites to the companies which receive and process it. policyXray is the first, and currently only, tool capable of auditing website privacy policies in order to evaluate disclosure of data transfers to specific parties. Both tools are highly resource efficient, allowing them to analyze millions of data flows and operate at a scale which is normally reserved for the companies collecting data. In short, these tools rectify the existing information asymmetry between the OBA industry and the public by leveraging the tools of mass surveillance for socially-beneficial ends. The research presented herein allows many specific existing social-normative concerns to be explored using empirical data in a way which was not previously possible. The impact of OBA on three main areas is investigated: regulatory norms, medical privacy norms, and norms related to the utility of the press. Through an examination of data flows on one million websites, and policies on 200,000 more, it is found in the area of regulatory norms that well-established Fair Information Practice Principles are severely undermined by the self-regulatory “notice and choice” paradigm. In the area of informational norms related to personal health, an analysis of data flows on 80,000 pages related to 2,000 medical conditions reveals that user health concerns are shared with a number of commercial parties, virtually no policies exist to restrict or regulate the practice, and users are at risk of embarrassment and discrimination. Finally, an analysis of 250,000 pages drawn from 5,000 U.S.-based media outlets demonstrates that core values of an independent and trustworthy press are undermined by commercial surveillance and centralized revenue systems. This surveillance may also transfer data to government entities, potentially resulting in chilling effects which compromise the ability of the press to serve as a check on power. The findings of this dissertation make it clear that current approaches to regulating OBA based on “notice and choice” have failed. The underlying “choice” of OBA is to sacrifice core social values in favor of increased profitability for primarily U.S.-based advertising firms. Therefore, new regulatory approaches based on mass surveillance of corporate, rather than user, behaviors must be pursued. Only by resolving the information asymmetry between the public, private corporations, and the state may social norms be respected in the online environment.